18 Fun Anniversary Ideas in Boston To Celebrate In Style

Anniversaries should always be celebrated with as much fun as style! That might mean dressing your best for a rooftop cocktail bar, taking a tour of Old Town Boston, or even doing both of these things and more besides! All you need are a few ideas to get your anniversary day started. That’s where we at Peerspace come in; we collect event ideas and venues to go along with the party! So do take a moment to explore some of our favorite anniversary ideas in Boston with us! 

1. Plan a picnic lunch at the Boston Commons

With over 350 years of history, the Boston Commons is America’s oldest public park. The grounds are a beautiful and iconic place to bring your partner for a picnic lunch or dinner when the weather cooperates! With over 50 acres of space, it isn’t too difficult to find a quiet place where you can enjoy a meal and drinks together. Afterwards, take them shopping at some of the stores within close walking distance of the Commons!

2. Enjoy a romantic dinner in a private venue

A dinner for two is one of the most traditional ways of celebrating any anniversary date. You could book a table for two at one of your favorite restaurants. Boston has one of the East Coast’s finest food scenes, after all. Or you could make the occasion extra special and private by reserving a loft, dining hall, rooftop venue, or other space for the evening.

Did you know that Peerspace has hundreds of dinner venues in Boston that would be perfect for a romantic dinner? Have you seen this wine–tasting space in Lynn, MA? The rental includes not just a beautiful event space but an expert sommelier to guide you through the finer points of choice wines!

3. Take a food tour of Central Square

Are you looking for an anniversary idea in Boston that is a fun experience as much as a meal or celebration? How about taking a food tour of Central Square with Off The Beaten Path? They offer public and private food tours where you get to explore the best of a particular Boston neighborhood. From pizza in Harvard Square to Lebanese in Jamaica Plain, you are sure to discover something new on a food tour!

4. Book a DIY crafts night

How about an anniversary idea in Boston that lets you leave with a piece of original art? Sculpt and paint some pottery that will last decades with The Clay Room for your upcoming anniversary! You can either make your own pieces or choose from what they have pre-fired and ready for painting. Use any of the 56 different colors in stock to make truly original art to take home and display.

Don’t forget to take lots of photos as you celebrate your anniversary! These sweet anniversary photoshoot ideas to celebrate the milestone can show you how.

5. Visit the New England Botanic Garden

Looking for an outdoor anniversary idea in Boston? Take a short drive to the New England Botanic Garden! Voted one of the nation’s top Botanic Gardens in 2023 by TravelAwaits, the New England gardens feature conservatories, seasonal floral displays, and endless opportunities for photos, reading, learning about plant conservation, and much more! 

6. Learn at the Museum of Fine Arts

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As Boston’s largest and oldest art institution, the Museum of Fine Arts is a must-see for all art aficionados! Exhibits rotate in and out of the collection and cover everything from Impressionist paintings to Asian calligraphy. If you want to make your anniversary bash a big party then consider one of The MFA’s private event spaces! From the Calderwood Courtyard to one of two spacious auditoriums, MFA offers guests the opportunity to appreciate fine art and party under a single roof!

7. Check out the New England Aquarium

With thousands of animals on display, the New England Aquarium is a must-see for conservation lovers! The Aquarium has multiple exhibits that concentrate on specific regions of the world, including the Amazon Rainforest and Olympic Coast Sanctuary. You can even pet sharks and rays at the Touch Tank or book exclusive behind-the-scenes experiences where you can meet harbor seals and ask questions of marine mammal trainers! 

8. Take a trolley tour of Old Town Boston

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Did you know that the trolleys are still running in Boston? You can get around Old Town Boston flexibly and affordably with a trolley tour! You’ll be riding with an expert guide who will give insights into the most interesting points of Boston’s history. What’s more, you can hop on and off the trolley as you like to explore each point of interest, only to catch the next trolley that goes by to see more of Old Town Boston! 

9. Go shopping at Quincy Market

Quincy Market has been a popular shopping destination in Boston for nearly 200 years! From fresh produce to arts and crafts, Quincy Market is a wonderful place to spend an afternoon browsing for something special. There are actually three market buildings close to one another: Quincy Market, the North Market, and the South Market. The beautiful architecture and regular performances draw as many people as the shopping opportunities!

10. Host a movie night for two

How about a movie night as an anniversary idea in Boston? With the amenities the city offers, though, you don’t even have to share a theater with the general public. Not when Peerspace has private venues where you can bring your own movies, snacks, and drinks to celebrate in complete privacy. For example, check out this private movie theater in Readville! From the Ultra High Def 4K Projector to the eight ceiling-mounted speakers, you won’t find a better cinema experience outside of a public theater!

11. Take an amphibious tour of Boston

Trolley tours, which we mentioned above, give you major insights into the downtown scene. But did you know that you can explore Boston from the water as easily as on land? Take a Boston Duck Tour, where you’ll be on a bus that takes you on a journey from the State House to coasting along the Charles River! 

12. Book a paint & sip class

Get creative over a few drinks with a paint-&-sip class! These events can include themes where you paint a specific scene, like sunsets or the city skyline. Other paint and sip classes might be about making selfies, painting a model, or freestyle painting. And don’t forget to BYOB or pick up a glass from the venue!  Celebrate your anniversary together with not only an experience but also some artwork you can hang up in your home.

13. Take a swan boat ride

The Boston Public Gardens is home to the swan boats, one of the city’s most iconic experiences! They have been in operation since 1877; unlike other cities with pedal boats, you don’t have any hard work to do. There is a driver who does all of the pedaling for you, leaving you free to enjoy being out on the water with your partner! You can take a swan boat ride any day from April to September!

14. Head to an arcade bar

Are you looking for an anniversary idea in Boston that is a little bit competitive? Take your partner to a video game arcade for some fun! Arcades only get better over time as more games become classics. Yet you will still find childhood favorites to enjoy alongside newer games. Arcade bars are even more fun since they function as full-service restaurants and bars where you can enjoy a drink as you hunt for more quarters! From lobster rolls to champagne cocktails, F1 Arcade is our pick for an unforgettable anniversary race gaming night in Boston!

Love the idea of a competition-fueled anniversary night? Then you need to also check out these creative couples game night ideas!

15. Try high-end dining at a nice restaurant

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Boston’s food scene is one of the best in the country so why not enjoy an anniversary evening together at a high-end restaurant? For a city that is world-famous for high-quality seafood, it’s hard to pick our favorite, but it just might be the Boston Sail Loft Cafe & Bar! If you’d prefer more turf than surf, check out Abe & Louie’s Steakhouse, a Best of Boston Winner for 3 years!   

16. See the Boston Public Library

Like many of Boston’s most historic venues, the Public Library is a nationwide first; in this case, young America’s first publicly funded free library! It opened in 1858 and now houses over 20 million items in its collection. The Boston Public Library is also an architectural wonder, with a stunning Grand Staircase and French paintings from master muralist Pierre Puvis de Chavannes on display (which can’t be seen anywhere else outside of France). The Tea Lounge even serves literary-themed cocktails and other beverages! 

17. Walk together along the Charles River Esplanade

The three-mile, 64-acre Charles River Esplanade Park is a wonderful walk to enjoy together any time of the year! You can do all kinds of outdoor activities here, like riding bikes together, enjoying a picnic lunch, or renting a kayak for some paddling!

18. Go ice skating at the Boston Commons Frog Pond

Winter doesn’t mean that outdoor activities have to come to an end. Not when you could head to the Boston Commons Frog Pond for some ice skating! Boston is rated as one of the top cities in the country as a winter destination so rent some skates and head outdoors for a winter anniversary event! 

Anniversary ideas in Boston: conclusion

From international cuisine to trolley tours, Boston has endless opportunities to enjoy an anniversary celebration together! We hope some of our fun anniversary ideas in Boston have inspired you. And while you are here, don’t discount the many private party venues in Boston that Peerspace offers for a more intimate celebration! 

Find unique event spaces in Boston for your date on Peerspace